Hydrochloric Acid → HCID 66906212, compound

HRID 1689623Notes

Reaction equation

HRID 1689623 reaction equation
Cl.C(O[CH:5]=[CH:6][C:7]1[N:8]([C:18]2[N:19]=[CH:20][N:21]=[C:22]([NH2:25])[C:23]=2[N:24]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])C.C([O-])([O-])=[O:27].[K+].[K+].CO>C1COCC1.C(Cl)Cl>[C:6]([C:7]1[N:8]([C:18]2[N:19]=[CH:20][N:21]=[C:22]([NH2:25])[C:23]=2[N:24]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])(=[O:27])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 66906744HCID 66906744, compound

Product 1

HCID 66906212HCID 66906212, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 M HCl (10 ml) was added to a solution of 8-ethoxyvinyladenosine (17k) (1.48 g, 4.37 mmol) in THF (40 ml) and the solution stirred at room temperature for 20 h. Aqueous K2CO3 was added to neutral pH and the mixture applied directly onto a flash chromatography silica gel column which was developed with 15% MeOH in CH2Cl2; yield 1.17 g (87%). 1H NMR: (300 MHz, DMSO-d6); δ 2.72 (3H, s, COCH3), 3.52-3.71 (2H, m, H-5′), 3.94-3.96 (1H, m, H-4′ el. H-3′), 4.10-4.23 (1H, m, H-3′ or H-4′), 4.94 (1H, m, H-2′), 5.11 (1H, d, J 4.4 Hz, 3′-OH), 5.24 (1H, d, J 6.1 Hz, 2′-OH), 5.56-5.59 (1H, m, 5′-OH), 6.76 (1H, d, J 6.5 Hz, H-1′), 7.87 (2H, s, NH2), 8.21 (1H, s, H-2). 13C NMR: (75 MHz, DMSO-d6); δ 27.9 (CH3), 62.3 (C-5′), 70.9/72.0 (C-2′, C-3′), 86.3/89.3 (C-4′, C-1′), 118.7 (C-5), 143.7/150.5/154.7/157.7 (C-6, C-8, C-2, C-4), 191.7 (CO).

Sources & evidence

ORD record
ord-ae5ec47c2ecf444d98ecaff96d5ad874
Source dataset
uspto-grants-2012_04
Patent number
US08153609B2

Reaction notes

Loading…